Abstract
A new polymerization reaction with a Pd(0) catalyst has been explored, in which polyamines (linear and cyclic) having amino groups in the main chains are produced. Two components of monomeric, compounds are employed; the one is a bifunctional allylic compound and the other is amine. As the amine components, tosylated amines are employed, too, to produce the corresponding tosylated derivatives of polyamine. A kind of polycondensation proceeded via a π-allyl palladium intermediate. The monomer structure and the character of the catalyst influence the proportion between linear and cyclic products.
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References
J. Tsuji, “Organic Synthesis with Palladium Compounds,” Springer-Verlag, Berlin, Heiderberg, and New York, 1980.
R. F. Heck “Palladium Reagents in Organic Syntheses,” Academic Press, London, 1985.
M. Suzuki, K. Sho, J.-C. Lim, and T. Saegusa, Polym. Bull., 21, 415 (1989).
M. Suzuki, J.-C. Lim, and T. Saegusa, Macromolecules, 23, 1574 (1990).
M, Suzuki, S. Sawada, and T. Saegusa, Macromolecules, 22, 1505 (1989).
“Polymeric Amines and Ammonium Salts,” E. J. Goethals, Ed., Pergamon Press, Oxford, 1980.
F. Chavez and A. D. Sherry, J. Org. Chem., 54, 2990 (1989), and references cited therein.
Ref. 1.
J. Tsuji, J. Synth. Org. Chem. Jpn., 41, 619 (1983).
Y. Ducharme, S. Latour, and J. D. Wuest, Organometallics, 3, 208 (1984).
T. Ukai, H. Kawazura, and Y. Ishii, J. Organometal. Chem., 65, 253 (1974).
K. E. Atkins, W. E. Walker, and R. M. Manyik, Tetrahedron Lett., 3821 (1970).
K. Osakada, T. Chiba, Y. Nakamura, T. Yamamoto, and A. Yamamoto, J. Chem. Soc., Chem. Commun., 1589 (1986).
T. Tsuda, Y. Horii, Y. Nakagawa, T. Ishida, and T. Saegusa, J. Org. Chem., 54, 977 (1989).
The reaction dimethyl 2-butenylene dicarbonate with some ditosylated diamines also produced cyclic products: T. Tsuda, T. Kiyoi, and T Saegusa, J. Org. Chem., 55, 3388 (1990).
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Suzuki, M., Lim, JC., Oguni, M. et al. Polycondensation Catalyzed by Palladium Complex III. Syntheses of Linear Polyamines and Cyclic Oligoamines via π-Allyl Palladium Intermediates. Polym J 22, 815–825 (1990). https://doi.org/10.1295/polymj.22.815
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DOI: https://doi.org/10.1295/polymj.22.815